Trinitrochlorobenzene
| Structural formula | |||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
|||||||||||||||||||
| General | |||||||||||||||||||
| Surname | Trinitrochlorobenzene | ||||||||||||||||||
| other names |
|
||||||||||||||||||
| Molecular formula | C 6 H 2 ClN 3 O 6 | ||||||||||||||||||
| Brief description |
light yellow crystal needles |
||||||||||||||||||
| External identifiers / databases | |||||||||||||||||||
|
|||||||||||||||||||
| properties | |||||||||||||||||||
| Molar mass | 247.55 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
||||||||||||||||||
| density |
1.797 g cm −3 (20 ° C) |
||||||||||||||||||
| Melting point |
83 ° C |
||||||||||||||||||
| solubility |
|
||||||||||||||||||
| safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
The trinitrochlorobenzene ( 2,4,6-trinitrochlorobenzene , picryl chloride ) is a solid chemical compound with explosive properties. It is derived from both chlorobenzene and nitrobenzene . The name picryl chloride comes from the early days of organic chemistry (19th century), as the synthesis at that time took place via the reaction of picric acid with phosphorus pentachloride .
presentation
Trinitrochlorobenzene can be prepared by nitration of 2,4-dinitrochlorobenzene by nitrating acid (65% nitric acid and 98% sulfuric acid are shown). The reaction mechanism corresponds to an electrophilic aromatic substitution .
The compound can also be obtained by reacting pyridinium picrate with phosphorus oxychloride .
properties
Trinitrochlorobenzene forms pale yellow crystal needles that melt at 83 ° C. The enthalpy of fusion is 73.3 kJ kg −1 . Vapor pressure data are known for the melt .
Vapor pressure of the melt temperature in ° C 83 100 150 200 270 pressure in mbar 0.05 0.2 2 12.5 100
Trinitrochlorobenzene is an explosive substance within the meaning of the Explosives Act . Important explosion indicators are:
Important explosion-relevant properties Oxygen balance −45.3% Nitrogen content 16.98% Lead block bulge 31.5 cm 3 g −1 Detonation velocity 7200 m · s −1 Deflagration point 395-397 ° C Sensitivity to impact 16 Nm Rubbing sensitivity no reaction up to 355 N pin load
Reactions
Trinitrochlorobenzene reacts with many nucleophilic compounds by substituting the chlorine atom. With aqueous ammonia solution, 2,4,6-trinitroaniline is formed . The reaction with hyrazine hydrate gives 2,4,6-trinitrophenyl hydrazine , which is used as an analytical reagent for the detection of ketones and aldehydes.
The mentioned substitution reactions proceed according to an addition-elimination mechanism . The old comparison with the carboxylic acid chlorides is justified because in both cases there is a nucleophilic substitution on the unsaturated carbon atom, which in principle takes place via intermediate stages with sp 3 -hybridized carbon. The Meisenheimer complexes were discovered during the reaction with alkali alcoholates .
use
As an explosive, the compound has similar properties to trinitrotoluene , and even exceeds it in terms of explosiveness. Nevertheless, it is rarely used in practice.
Individual evidence
- ↑ a b c d Explosivstoffe , Wasag-Chemie, Essen 1961, p. 166.
- ↑ a b c d e Entry on 2-chloro-1,3,5-trinitrobenzene in the GESTIS substance database of the IFA , accessed on March 26, 2020(JavaScript required) .
- ↑ Entry on 2-chloro-1,3,5-trinitrobenzene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ a b c d e f g h i j J. Köhler, R. Meyer, A. Homburg: Explosivstoffe , tenth, completely revised edition, Wiley-VCH, Weinheim 2008, p. 332, ISBN 978-3-527-32009 -7 .
- ↑ Explosives Act, Appendix I, List of Explosive Substances ( BGBl. 1975 I p. 853 ), to which the law is to be applied in full.
literature
- Beilstein's Handbook of Organic Chemistry, Volume 5 (main work p. 273; 1st supplementary work p. 140; 2nd supplementary work p. 205).